Trifluoromethanesulfonic acid → 5-Iodoisatin

HRID 348404Notes

Reaction equation

HRID 348404 reaction equation
[I:1]N1C(=O)CCC1=O.Cl[C:10]1[CH:18]=[C:17]2[C:13]([C:14](=[O:20])[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.S(O)(C(F)(F)F)(=O)=O>>[I:1][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:10]=1)[NH:16][C:15](=[O:19])[C:14]2=[O:20]

Participants

4

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 2413316-Chloroindoline-2,3-dione

Product 1

HCID 886955-IodoisatinYield 99.6%

Procedure

N-Iodosuccinimide (8.68 g, 38.6 mmol) was added to a stirred mixture of 6-chloro-isatin (6.98 g, 38.6 mmol) and TfOH (120 g) at 0° C. under N2. Ice-bath was removed and stirring at room temperature was continued for 19 h. The mixture was poured to ice-water. The precipitate was collected by filtration, washed with water (until pH˜7), and dried to give 6-chloro, 5-iodo-isatine (10.5 g) as a 95% pure (1H NMR, 400 MHz), orange solid: 1H NMR (DMSO-d6) 7.10 (s, 1 H), 7.96 (s, 1 H), 11.21 (s, 1 H); ms 305.9 (M−H+).

Workup

  1. customIce-bath was removed
  2. additionThe mixture was poured to ice-water
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (until pH˜7)
  5. customdried

Sources & evidence

ORD record
ord-1e99d96ea50e45e093565d61d5ea3249
Source dataset
uspto-grants-2007_02
Patent number
US07176314B2

Reaction notes

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